US7704286B2 - Reactive dyestuff composition and their use - Google Patents

Reactive dyestuff composition and their use Download PDF

Info

Publication number
US7704286B2
US7704286B2 US11/300,461 US30046105A US7704286B2 US 7704286 B2 US7704286 B2 US 7704286B2 US 30046105 A US30046105 A US 30046105A US 7704286 B2 US7704286 B2 US 7704286B2
Authority
US
United States
Prior art keywords
formula
dye
composition
compound
present
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired - Fee Related, expires
Application number
US11/300,461
Other languages
English (en)
Other versions
US20070044256A1 (en
Inventor
Huei-Chin Huang
Ya-Chi Tseng
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Everlight USA Inc
Original Assignee
Everlight USA Inc
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Everlight USA Inc filed Critical Everlight USA Inc
Assigned to EVERLIGHT USA, INC. reassignment EVERLIGHT USA, INC. ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: HUANG, HUEI-CHIN, TSENG, YA-CHI
Publication of US20070044256A1 publication Critical patent/US20070044256A1/en
Application granted granted Critical
Publication of US7704286B2 publication Critical patent/US7704286B2/en
Expired - Fee Related legal-status Critical Current
Adjusted expiration legal-status Critical

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
    • C09B67/0033—Blends of pigments; Mixtured crystals; Solid solutions
    • C09B67/0046—Mixtures of two or more azo dyes
    • C09B67/0047—Mixtures of two or more reactive azo dyes
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
    • C09B67/0033—Blends of pigments; Mixtured crystals; Solid solutions
    • C09B67/0046—Mixtures of two or more azo dyes
    • C09B67/0051—Mixtures of two or more azo dyes mixture of two or more monoazo dyes
    • C09B67/0052—Mixtures of two or more reactive monoazo dyes

Definitions

  • the present invention relates to dye compositions and the use thereof and, more particularly, to a yellow reactive dye composition and the use thereof on special textile finishing processes.
  • the reactive dyestuffs used for dyeing or printing cellulose fiber materials or cellulose containing fibers particularly need high quality such as the properties of leveling, reproducibility, solubility, fastness etc.
  • the inventor of the present invention found a dye composition characterized with fine properties in ghosting fastness, compatibility, photochromism and build-up can be formed by mixing together another dyestuff with pyrazoline azo dyestuff. They are not only having superior characteristics of fastness properties, the dye compositions of the present invention are also capable of dyeing with a broad color gamut, and economic in achieving various fastness properties.
  • the present invention provides a dye composition, which has good dyeing properties such as ghosting fastness, color compatibility, photochromism and build-up.
  • the dye compositions of the present invention are economic in dyeing pale shade and achieving various fastness properties as well.
  • the dye compositions of the present invention can be mixed with conventional dyestuffs to overcome the drawbacks of build-up, compatibility, and limited color gamut, from that providing the market with a superb compatibility, ghosting fastness, build-up and photochromism combination.
  • the dye composition of the present invention comprising:
  • component (a) is present in an amount ranging from 95% to 5% by weight relative to total weight of the composition
  • component (b) is present in an amount ranging from 5% to 95% by weight relative to total weight of the composition.
  • the compound of formula (I) of the dye composition of the present invention preferably it is the compound of the following formula (Ia):
  • the compound of formula (II) of the dye composition of the present invention preferably it is the following compound of formula (IIa):
  • the compound of formula (III) of the dye composition of the present invention preferably it is the following compound of formula (IIIa):
  • the compound of formula (IV) of the dye composition of the present invention preferably it is the following compound of formula (IVa);
  • (R 4 ) 0 ⁇ 3 is 0 to 3 the same or different groups selected from the group consisting of halogen, carboxyl, sulfo, C 1-4 alkyl and C 1-4 alkoxyl;
  • the compound of formula (I) of the dye composition of the present invention is the following compound of formula (Ib);
  • the compound of formula (II) of the dye composition of the present invention is the following compound of formula (IIb);
  • the compound of formula (III) of the dye composition of the present invention is the following compound of formula (IIIb);
  • the compound of formula (IV) of the dye composition of the present invention is the following compound of formula (IVb):
  • the compound of formula (I) of the dye composition of the present invention most preferably it is the following compound of formula (I-1):
  • the compound of formula (II) of the dye composition of the present invention most preferably it is the following compound of formula (II-1):
  • the compound of formula (III) of the dye composition of the present invention most preferably it is the following compound of formula (III-1):
  • the compound of formula (IV) of the dye composition of the present invention most preferably it is the following compound of formula (IV-1):
  • the dye compositions of the present invention are suitable for dyeing materials that contain either cellulose fibers, such as cotton, artificial cotton, linen, and artificial linen, or synthetic polyamide, such as wool, silk, and nylon.
  • Dyeing materials with dye compositions above-mentioned will achieve excellent properties, especially in build-up, color compatibility, photochromism and ghosting fastness.
  • the dye compositions of the present invention can be mixed with conventional dyestuffs to overcome the drawbacks of discoloring, color distortion, and compatibility, from that providing a superb ghosting fastness and photochromism combination.
  • conventional dyestuffs to overcome the drawbacks of discoloring, color distortion, and compatibility, from that providing a superb ghosting fastness and photochromism combination.
  • the dye compositions of the present invention improve the light fastness, ghosting fastness, as well as other problems such as poor dyeing compatibility and discoloration of the golden-yellow color, particularly in dyeing extremely pale shades, where when the red and/or blue dyestuffs having good light fastness and ghosting fastness are exposed under light and tested with ghosting fastness test along with the dye compositions of the present invention not only the hue demonstrates small color distortion while little discoloration are observed.
  • the compound of formula (IV) of the present invention composition may be prepared by the following methods.
  • the dyestuff of formula (IV) of the present invention is the azo dye of the following formula (IVa):
  • D 1 and D 2 are defined the same as the aforementioned. More preferably it is the azo dye of the following formula (IVb):
  • the component (a) dye is present in an amount ranging from 99% to 1% by weight relative to total weight of the composition
  • the component (b) dye is present in an amount ranging from 1% to 99% by weight relative to total weight of the composition.
  • the component (a) dye is present in an amount ranging from 95% to 5% by weight relative to total weight of the composition
  • the component (b) dye is present in an amount ranging from 5% to 95% by weight relative to total weight of the composition.
  • the component (a) dye is present in an amount ranging from 90% to 10% by weight relative to total weight of the composition
  • the component (b) dye is present in an amount ranging from 10% to 90% by weight relative to total weight of the composition.
  • composition of the present invention can be prepared in many ways. For example by using separately prepared dye components and then mixing each dye together.
  • the way of mixing is by using a proper mixer, for example a ball and sand grinder.
  • individual dye with different components can make dye liquid through stirring or through control of conditions in each dye preparation to produce an ideal mixture.
  • separate dyes can be mixed together or mixed with other dyes.
  • the dye compositions of the present invention may be contained with inorganic salts (e.g. sodium sulfate or sodium chloride), dispersants (e.g. ⁇ -naphthalene sulfonic acid-formaldehyde condensation products, methyl naphthalene sulfonic acid-formaldehyde condensation products, acetyl amino naphthol based compounds, etc.), non-dusting agents (e.g. di-2-ethylhexyl terephthalate, etc.), pH buffer agents (e.g. sodium acetate, sodium phosphate, etc.), water softeners (e.g. polyphosphate, etc.), well-known dyeing assistants, and etc.
  • inorganic salts e.g. sodium sulfate or sodium chloride
  • dispersants e.g. ⁇ -naphthalene sulfonic acid-formaldehyde condensation products, methyl naphthalene sulfonic acid
  • the form of the dye compositions of the present invention is not necessary to limitation.
  • the dye compositions of the present invention can be in the form of powders, granules or liquids.
  • the compounds are expressed as free acid in the specification.
  • the dyestuffs of the present invention are manufactured, purified or used, they often exist in the form of water soluble salts, especially alkaline metallic salts, such as sodium salts, lithium salts, potassium salts or ammonium salts, and preferably sodium salts.
  • the dye compositions of the present invention can dye many kinds of fiber materials such as cellulose fiber materials and cellulose included fiber materials. These dye compositions can also be used to dye natural cellulose fibers and regenerated cellulose fibers, such as cotton, linen, jute, ramie, mucilage rayon, as well as cellulose based fibers.
  • the dyeing or printing of the reactive dye composition can be preceded by usual or known method.
  • Exhaustion dyeing is applied by using usual inorganic salts (e.g. sodium sulfate and sodium chloride) and well-known acid-binding agents (e.g. sodium carbonate, sodium hydroxide).
  • the amount of inorganic salts and alkali here is not important.
  • Inorganic salts and alkali can be added into the dyeing bath through traditional methods either by once or by several times.
  • dyeing assistants can be added, too.
  • the range of dyeing temperature is from 40° C. to 90° C.
  • the temperature for dyeing is from 50° C. to 70° C.
  • dye, alkali and customary auxiliaries are padded from the liquor through.
  • the padded, squeezed substrate is often rolled onto an A-frame and batched at room temperature to allow dye fixation to take place.
  • a continuous dyeing it can be divided into two different methods.
  • dye, alkali e.g. sodium carbonate or sodium bicarbonate
  • customary auxiliaries are padded from the liquor through, the padded, squeezed substrate was then dried by either baking or steam.
  • the substrate is padded through a dye solution bath, pre-dried, an alkali (e.g. sodium hydroxide or sodium silicate) bath, then dye fixed by either baking or steam.
  • alkali e.g. sodium hydroxide or sodium silicate
  • the composition of the present invention consists of good fixing capacity and very good build up capacity. Besides, the dye composition exhibits excellent color depth, level dyeing and wash off properties, as well as high solubility, high exhaustion and high fixation percentage. Therefore exhaustion dyeing can be applied under low dyeing temperature and during pad-steaming process only a short steaming time is required for the dye composition. The result has high fixation yield as well the unfixed regions can be easily washed off, mean while difference between tictorial yield and fixation yield is small, and only minor lost in soap wash can be detected.
  • the dye compositions of the present invention exhibit a wide range of colors and increase the dye affinity to cellulose fiber materials while dyeing or printing, and can be used in either acid or base dyeing environments.
  • the dyed cellulose fiber materials have excellent properties of light fastness, ghosting fastness, and wet fastness, e.g. wash fastness, water fastness, seawater fastness, cross-dyeing fastness, and perspiration fastness, as well as pleating fastness, ironing fastness, and rubbing fastness. Therefore, the present invention is a valuable reactive yellow dye for cellulose fibers in the present dyeing industry.
  • the dye compositions have the materials dyed with excellent properties and resulting outstanding build-up, photochromism, ghosting fastness and light fastness.
  • the general reactive dyestuff will not meet the requirements of the extremely pale shade and mixture market any more.
  • the dye compositions of the present invention exhibit better ghosting fastness in pale shade, and particularly demonstrating excellent compatibility, photochromism and ghosting fastness in mixture of extremely pale shade, thereby allowing this invention to fit in with the requirements and expectations of market.
  • Preparing dyestuffs of formula (I-1) and formula (II-1) as described above Take 90 weight parts of formula (I-1) and 10 weight parts of formula (II-1) and mixed completely to form a dye composition.
  • Preparing dyestuffs of formula (I-1) and formula (II-1) as described above Take 75 parts of formula (I-1) and 25 parts of formula (II-1) and mixed completely to form a dye composition.
  • Preparing dyestuffs of formula (I-1) and formula (II-1) as described above Take 60 parts of formula (I-1) and 40 parts of formula (II-1) and mixed completely to form a dye composition.
  • the golden yellow dye product having high sale volume in the market and widely use is selected. Such as from the color index, dye serial number including C.I. reactive yellow dye No. 176, C.I. reactive orange dye No. 107, C.I. reactive yellow dye No. 84 or mixture of is used and referenced for comparison in the dye property testing of the present invention.
  • First dye liquors are prepared, wherein each 80 mL liquor respectively has a concentration of 0.5% on the weight of the fabric (o.w.f). After that inorganic neutral salt is added, and then dyeing of the un-mercerized cloths made of pure cotton is started. The un-mercerized cotton cloths are soaked in the dye liquors. At the same time, dyeing of the dyestuffs is started at 60° C. and then the dyestuffs started diffusing to adhere the cloths with the aid of a horizontal shaker, which is followed by adding an alkali agent that made the dyestuffs react with fiber completely to achieve firm adherence. The resulting dyed cloths are water cleaned, soaping off, and tumbled-dried to form finish products.
  • the samples are soaked in water, where the excess water is removed after while maintaining the samples with a humidity of 100%, after both the printed and unprinted samples are folded and placed in a sublimating fastness device under 120° C. ⁇ 30 min, lastly with the use of AATCC EP1 the processed samples are proceeded with color distortion comparison.
  • Trichromatic mixture composition 0.5% concentration dye liquors of yellow, red and blue (o.w.f) ⁇ Example 1 4-5 ⁇ Everzol Red 3BS ⁇ Everzol Blue BRF ⁇ Example 2 4-5 ⁇ Everzol Red 3BS ⁇ Everzol Blue BRF ⁇ Example 3 4-5 ⁇ Everzol Red 3BS ⁇ Everzol Blue BRF ⁇ Example 4 3-4 ⁇ Everzol Red 3BS ⁇ Everzol Blue BRF ⁇ Example 5 3-4 ⁇ Everzol Red 3BS ⁇ Everzol Blue BRF ⁇ Example 6 3-4 ⁇ Everzol Red 3BS ⁇ Everzol Blue BRF ⁇ Example 7 3-4 ⁇ Everzol Red 3BS ⁇ Everzol Blue BRF ⁇ Example 8 3-4 ⁇ Everzol Red 3BS ⁇ Everzol Blue BRF ⁇ Example 9 3-4 ⁇ Everzol Red 3BS ⁇ Everzol Blue BRF ⁇ C.I. reactive yellow dye No.
  • the ghosting of the dyed products of the aforementioned examples 1-9, comparative examples 1-3 and the trichromatic mixture dye composition of yellow, red and blue are tested by discoloring test.
  • Datacolor Spectraflash-SF450 color spectrometer is used to examine the difference between the before and after dyeing strength and extend of discoloration, where the higher grade level with minimum changes are preferred.
  • the dye compositions of examples 1-9 of the present invention demonstrate high level hue strength with minimum changes, such that they indicate the preferred ghosting fastness can go up to level 3 and above.
  • the trichromatic mixture of yellow, red and blue comprising the components of the dye compositions of examples 1-9 of the present invention demonstrates high level hue strength with minimum changes, such that they indicate the preferred ghosting fastness can go up to level 3 and above. From the above, the dye compositions of examples 1-9 of the present invention are superior with respect to other golden-yellow dyestuffs.
  • First dye liquors are prepared, wherein each 80 mL liquor respectively has a concentration of 0.5%. After that inorganic neutral salt is added, and then dyeing of the un-mercerized cloths made of pure cotton is started. The un-mercerized cotton cloths are soaked in the dye liquors. At the same time, dyeing of the dyestuffs is started at 60° C. and then the dyestuffs started diffusing to adhere the cloths with the aid of a horizontal shaker, which is followed by adding an alkali agent that made the dyestuffs react with fiber completely to achieve firm adherence. The resulting dyed cloths are water cleaned, soaping off, and tumbled-dried to form finish products.
  • the aforementioned dye products are placed in a dark room for two hours, and then color test is carried out with the use of Datacolor Spectraflash-SF450 color spectrometer.
  • Color test is carried out with the use of Datacolor Spectraflash-SF450 color spectrometer.
  • D 65 light source Datacolor Tru-Vue ⁇ D 65
  • color test is proceeded with Datacolor Spectraflash-SF450 color spectrometer, the discoloration of the before and after test is compared.
  • the dye products of the aforementioned examples 1-9, comparative examples 1-3 and the trichromatic mixture dye composition of yellow, red and blue are tested by exposing under D 65 light.
  • Datacolor Spectraflash-SF450 color spectrometer is used to examine the discoloration extend between the before and after test, where it is preferred to have a low ⁇ E with minimal discoloration.
  • the dye compositions of examples 1-9 of the present invention demonstrate low ⁇ E when exposed to D 65 light, such that they indicate minimal discoloration and good photochronmsm.
  • the trichromatic mixture of yellow, red and blue comprising the components of the dye compositions of examples 1-9 of the present invention demonstrates a ⁇ E below 0.2 when exposed to D 65 light, such that it indicates the dye composition of examples 1-9 of the present invention have low discoloration with minimal changes, and is preferred over other golden yellow dyestuffs.
  • the dye compositions of the present invention are general dye compositions suitable for dyeing cellulose fibers. They can be used to dye cellulose fibers with various dyeing methods, such as exhaustion dyeing, printed-dyeing, or continuous dyeing that are commonly used in the dyeing of reactive dyestuffs.
  • the dye compositions of the present invention are water-soluble dyestuffs that have a highly commercial value.
  • the dye compositions of the present invention can obtain dyeing results with excellent properties in all aspects, especially in washing off, build-up, levelness, photochromism, ghosting fastness and light fastness.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Chemistry (AREA)
  • Coloring (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Macromonomer-Based Addition Polymer (AREA)
US11/300,461 2005-08-31 2005-12-15 Reactive dyestuff composition and their use Expired - Fee Related US7704286B2 (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
CNB2005100939788A CN100413930C (zh) 2005-08-31 2005-08-31 反应性染料组成物及其应用
CN200510093978.8 2005-08-31
CN200510093978 2005-08-31

Publications (2)

Publication Number Publication Date
US20070044256A1 US20070044256A1 (en) 2007-03-01
US7704286B2 true US7704286B2 (en) 2010-04-27

Family

ID=37571848

Family Applications (1)

Application Number Title Priority Date Filing Date
US11/300,461 Expired - Fee Related US7704286B2 (en) 2005-08-31 2005-12-15 Reactive dyestuff composition and their use

Country Status (5)

Country Link
US (1) US7704286B2 (de)
EP (1) EP1760117B1 (de)
CN (1) CN100413930C (de)
AT (1) ATE455154T1 (de)
DE (1) DE602006011688D1 (de)

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE102008054404A1 (de) * 2008-12-09 2010-06-10 Dystar Textilfarben Gmbh & Co. Deutschland Kg Faserreaktive Azofarbstoffe und Farbstoffmischungen, Verfahren zu ihrer Herstellung und ihre Verwendung
US8349029B2 (en) 2008-12-09 2013-01-08 Dystar Colours Deutschland Gmbh Fiber-reactive azo dyes and dye mixtures, preparation thereof and use thereof
TWI411650B (zh) 2009-07-15 2013-10-11 Everlight Chem Ind Corp 具有ｎ－烷胺基的新型反應性染料
CN102206428B (zh) * 2010-03-30 2014-05-28 明德国际仓储贸易(上海)有限公司 具有n-烷胺基的反应性染料
CN107974103B (zh) * 2017-12-04 2020-01-21 湖北华丽染料工业有限公司 一种复合活性黄染料
CN117701030B (zh) * 2023-12-11 2026-03-27 浙江亿得新材料股份有限公司 一种光敏性好的黄色活性染料组合物及制备方法、应用
CN117587628A (zh) * 2023-12-11 2024-02-23 中山市华帛纺织科技有限公司 一种遇光变色符合抗菌锦纶纱线配方及其制备方法

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS57141455A (en) 1981-02-26 1982-09-01 Nippon Kayaku Co Ltd Reactive monoazo compound and dyeing by using the same
EP0072557A2 (de) 1981-08-19 1983-02-23 Hoechst Aktiengesellschaft Wasserlösliche Azoverbindungen, Verfahren zu ihrer Herstellung und ihre Verwendung als Farbstoffe
JPH04370157A (ja) * 1991-06-19 1992-12-22 Sumitomo Chem Co Ltd 反応染料組成物およびそれを用いる繊維材料或いは皮革の染色または捺染方法
US5849887A (en) * 1997-04-07 1998-12-15 Ciba Specialty Chemicals Corporation Mixtures of reactive dyes and their use
US7052521B2 (en) * 2004-02-25 2006-05-30 Everlight Usa, Inc. Dye composition and the use thereof
US7387647B2 (en) * 2004-11-29 2008-06-17 Everlight Usa, Inc. Dye composition and the use thereof

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
TW446734B (en) * 1997-12-11 2001-07-21 Ciba Sc Holding Ag Process for dyeing or printing and novel reactive dyes
JP2004124053A (ja) * 2002-05-30 2004-04-22 Kyung-In Synthetic Corp 繊維反応性染料およびその製造方法
CN1257233C (zh) * 2002-11-01 2006-05-24 台湾永光化学工业股份有限公司 单偶氮反应性红色染料
US7259259B2 (en) * 2002-12-02 2007-08-21 Huntsman International Llc Reactive dyes, a process for their preparation and their use
EP1568738A3 (de) * 2004-02-25 2006-12-13 Everlight USA, Inc. Färbemittel und deren Verwendung

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS57141455A (en) 1981-02-26 1982-09-01 Nippon Kayaku Co Ltd Reactive monoazo compound and dyeing by using the same
EP0072557A2 (de) 1981-08-19 1983-02-23 Hoechst Aktiengesellschaft Wasserlösliche Azoverbindungen, Verfahren zu ihrer Herstellung und ihre Verwendung als Farbstoffe
JPH04370157A (ja) * 1991-06-19 1992-12-22 Sumitomo Chem Co Ltd 反応染料組成物およびそれを用いる繊維材料或いは皮革の染色または捺染方法
US5849887A (en) * 1997-04-07 1998-12-15 Ciba Specialty Chemicals Corporation Mixtures of reactive dyes and their use
US7052521B2 (en) * 2004-02-25 2006-05-30 Everlight Usa, Inc. Dye composition and the use thereof
US7387647B2 (en) * 2004-11-29 2008-06-17 Everlight Usa, Inc. Dye composition and the use thereof

Non-Patent Citations (3)

* Cited by examiner, † Cited by third party
Title
11300461-277574-EIC Search, completed by STIC on Nov. 21, 2008, dye structure search. *
Abstract of JP57141455. "Reactive Monoazo Compound and Dyeing by Using the Same" Data supplied from the esp@cenet database. *
English abstract of Akahori et al., accessed in Derwent, Acc. No. 1993-042634. *

Also Published As

Publication number Publication date
CN100413930C (zh) 2008-08-27
ATE455154T1 (de) 2010-01-15
EP1760117B1 (de) 2010-01-13
DE602006011688D1 (de) 2010-03-04
EP1760117A3 (de) 2007-07-25
EP1760117A2 (de) 2007-03-07
US20070044256A1 (en) 2007-03-01
CN1923906A (zh) 2007-03-07

Similar Documents

Publication Publication Date Title
US7704287B2 (en) Reactive red dye composition and application thereof
US7387647B2 (en) Dye composition and the use thereof
TWI462974B (zh) 反應性染料混合物及其於三色染色或印花方法中之用途
US6585782B2 (en) Mixtures of reactive dyes and their use
US7540883B2 (en) Reactive yellow dye composition
US20070044256A1 (en) Reactive dyestuff composition and their use
US7390889B1 (en) Trisazo reactive dyestuff compound
US7098319B2 (en) Disazo reactive dyestuffs containing the quaternary groups and their use
CN105542510A (zh) 一种活性黑染料组合物及染料制品
CN110128849B (zh) 一种黄色酸性染料组合物及其在纤维上的染色应用
US7052521B2 (en) Dye composition and the use thereof
KR20060085780A (ko) 신규한 반응성 적색 염료 및 이를 이용한 삼색 배합 염색
JP2762640B2 (ja) 反応染料混合物及びそれを用いる繊維材料の染色方法
CN100528972C (zh) 一种复合活性染料
CN102504582B (zh) 一种活性深蓝双偶氮染料及其制备方法
US7282070B2 (en) Reactive dye composition and the use thereof
CN110054910A (zh) 一种黑色活性染料组合物及其制备方法和应用
CN110128847B (zh) 一种蓝色酸性染料组合物及其在纤维上的染色应用
US6955693B2 (en) Dye composition and the use thereof
CN115304930A (zh) 一种活性染料组合物及染料制品
CN109796785B (zh) 一种活性蓝至黑色染料组合物和染料制品及其应用
EP1568738A2 (de) Färbemittel und deren Verwendung
KR0181491B1 (ko) 반응성 염료 및 이의 염료제제
US20060185102A1 (en) Reactive dyestuff composition and their use
US7666232B2 (en) Reactive trichromatic dye set

Legal Events

Date Code Title Description
AS Assignment

Owner name: EVERLIGHT USA, INC.,NORTH CAROLINA

Free format text: ASSIGNMENT OF ASSIGNORS INTEREST;ASSIGNORS:HUANG, HUEI-CHIN;TSENG, YA-CHI;REEL/FRAME:017373/0250

Effective date: 20051122

Owner name: EVERLIGHT USA, INC., NORTH CAROLINA

Free format text: ASSIGNMENT OF ASSIGNORS INTEREST;ASSIGNORS:HUANG, HUEI-CHIN;TSENG, YA-CHI;REEL/FRAME:017373/0250

Effective date: 20051122

FPAY Fee payment

Year of fee payment: 4

FEPP Fee payment procedure

Free format text: MAINTENANCE FEE REMINDER MAILED (ORIGINAL EVENT CODE: REM.)

LAPS Lapse for failure to pay maintenance fees

Free format text: PATENT EXPIRED FOR FAILURE TO PAY MAINTENANCE FEES (ORIGINAL EVENT CODE: EXP.)

STCH Information on status: patent discontinuation

Free format text: PATENT EXPIRED DUE TO NONPAYMENT OF MAINTENANCE FEES UNDER 37 CFR 1.362

FP Lapsed due to failure to pay maintenance fee

Effective date: 20180427